


The First Time

by CleverDame



Category: Supernatural
Genre: F/M, Loss of Virginity, Oral Sex, Vaginal Fingering, Vaginal Sex, Virginity, unprotected sex
Language: English
Status: Completed
Published: 2017-06-06
Updated: 2017-06-06
Packaged: 2018-11-09 15:03:13
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,027
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11107026
Author URL: https://archiveofourown.org/users/CleverDame/pseuds/CleverDame
Summary: Summary: You and Sam experience several sexual firsts together. Sam finds Dean’s advice useful.Warnings:  first time sex, unprotected sex, virgins (Sam and Reader), vaginal fingering, foreplay





	The First Time

“Like that?” Sam asks quietly, his voice and the catch of your own breath are the only sounds amid deafening silence. You wish you’d turned the radio on or something. His fingers are inside your panties, dancing hesitantly over you sex, neither of you know what exactly you’re doing.

You’ve been dating for three months now, practically a lifetime, and up until tonight you’ve only made out while letting him feel you up over your shirt…and two nights ago you dry humped in the back of his dad’s car, twisting in his lap until he made you stop, his face red and sweating.

Oh yeah, and the blowjob.

Now, you’re laid out on your living room couch in nothing but your underwear. Your mother is gone until tomorrow so what better time to take things further. Sam’s on his side, wedged between you and the back of the couch, running his hands over your body. “A little further,” you wiggle as his finger scoops up, pressing between soft flesh.

Sam closes his eyes, trying to remember the diagram in the book he read. According to that book, and his brother, all he needs to do is find this elusive little bump and you’ll be pleading him not to stop.

His index finger slides over your clit and you both feel it, you gasp as he flicks over it again watching in amazement as you close your eyes and tip your head back, “that’s it, right there, oh _Sam_.”

He’s never had a girl say his name like that before, all breathy and full of need, his cock manages to get even harder in his pants as you writhe up into his hand while he plays back and forth over this newfound sweet spot.

He tries to recall what Dean told him, he’d acted like he was disgusted as his brother gave him incredibly graphic instructions. He’d fallen asleep that night with Dean’s words reverberating in his head, trying to memorize all the specifics. He wants to make you feel good, wants to be able to give you the same pleasure you gave him last week when you sucked on his cock for the first time.

And he really wants you to let him have sex with you.

Replaying the details in his head he dips his finger down and into your pussy, where he finds that your incredibly wet, just like he hoped you’d be. He’s never touched a girl like this before and your body seems so much more complicated than his, he hopes he doing it right.

You moan, feeling his finger push inside you, coating with slick before moving back up and over your clit with easy movements that send shocks through your entire body. He grins at your reaction, thankful for the advice and looks hungrily at hard nipples that seem to be calling to him. He thinks about asking you if he can suck on them but remembers what Dean said: _girls like confidence._

So, with that in mind, he lowers his head to your breast and sucks a nipple into his mouth as his finger continues to work that little bundle of nerves. You moan so loud it makes him flinch, your hand knotting in his hair as he sucks a little harder, moving his finger a little faster.

“Sam,” you pant, tugging his head away from you breast with a pop.

“What’s wrong?” he asks wide-eyed, his hand stopping all movement.

“Will you, you know,” you blush, biting your lip as he looks at you bewildered, “will put your fingers inside me?”

“Yeah,” Sam whimpers and nods his head, as you slip your panties down your thighs.

He takes a deep breath and looks down, watching your legs fall wide as he rubs one finger between your folds, he begins to slide his index finger deeper when you grab his wrist, stopping him, “two, please.”

_Fuck._

He doesn’t say anything just uses his index and middle finger as he pushes up and into your wet cunt. He goes slow, waiting for you to stop him and when you don’t he just keeps moving until he’s sunk knuckle deep. You’re so warm and wet and tight that he thinks he might cream in his pants, he’s not sure he can even handle putting his dick in there.

He wiggles his fingers and you make incredible noises, breathing faster. He begins to pump his fingers in and out until he finds a steady rhythm, your hips moving in time with his hand, moaning with every thrust.

Dean’s voice pops into his head: _it’s all about her clit bud, doesn’t matter if your kissing, fucking or fingering her, just keep rubbing her clit and she’ll go crazy._

So he does.

He brings his thumb up to press over your clit while his fingers continue to move and you make a noise like he’s never heard before. “Oh, Oh, Sam, please don’t stop, I’m gonna…”

“It’s okay, I want to watch you,” he lowers his mouth, flicking his tongue over your nipple,with eyes open, intently observing where his hand’s doing work.

You come for the first time from anything other than humping a pillow, making the most wonderful strangled sounds. He feels your pussy pulse and contract around his hand, your whole body twitching and undulating as your orgasm overtakes you. You say his name over and over again; _Sam, Sam, Sam._

He’s pretty sure it’s the most beautiful thing he’ll ever hear.

He stays inside until your still and silent, then pulls out, resting his wet fingers on your stomach. He kisses you sweetly, his hips grinding into your side, the unmistakable bulge in his jeans straining for release. You drop your hand down to unbutton his fly, then unzip him. Sam shimmies his pants and boxers down as his cock springs free, bobbing as it rests warm over the side of you stomach.

“Can we, I mean…do you wanna have sex?” He trying to maintain an air of self assuredness, but in reality he’s so nervous he’s worried he might start shaking.

“I want to,” you whisper, tugging at his arm and pulling him on top of you, “but only if you love me.”

“I do!” Sam blurts out immediately, “I love you.” He looks down, settling between your legs with his dick poking your thigh, he means what he says. “Do you love me?”

“Yes, I love you so much,” you nod enthusiastically, heart feeling like it might burst.

You’re both too young to really know what love is, but in the moment this feels like what you imagine love should be like.  

“Are you ready?” he asks stroking his cock, the head poking where you’re already wet.

“Ahuh. Go slow, okay? Don’t hurt me.” You close your eyes, tipping your head back trying to prepare yourself. As you press small hands into the muscles of his chest he wonders if you can feel his heartbeat speed up in anticipation.

“I’m not gonna hurt you, I promise.” He brings his fingers down to your clit, you gasp in surprise as his pushes inside for the first time. He’s cognizant of keeping his thumb moving over your bud as he feels thin barrier of tissue just like he read about. He pushes forward, sinking balls deep as he pants, his breath catching in his throat. You cry out, muffled with you face pressed into his shoulder as your body stiffens. You clench down hard around his cock and it takes everything within him not to come right then and there.  You’re like tight, hot silk squeezing his cock, it’s better than he ever imagined. He wants to pull out fast and shove back in hard, feel you slide around him.

It’s doesn’t hurt as much as you thought it would, instead there’s only a moment of unpleasant tension that’s quickly replaced by the wonderful stretch of his dick.

“Are you okay?” He asks, dropping his head and pressing his nose into yours.

“It feels good,” you raise your hips upward, tugging at his arm, “you can move.”

Sam takes a deep breath propping himself up on his arms as he looks down, watching as he pulls out slowly, only his tip remaining inside. He’s coated in your slick, his cock shiny with a faint tinge of blood. You whine, making a noise that’s far from pained and he eases back inside, closing his eyes.

He starts to move faster, his hips rolling into you as he finds a pace makes his balls tingle. The noises you’re making are mind blowing and his chest feels tight with lust as your hips begin to move with his, meeting him halfway, taking his cock in a way he never previously dreamed possible.

You reach down to rub your clit like he did, slender fingers gliding in a way that seems to make him feel even better inside you.

“Sam!” He thrusts forward a few more times and you come again, sweet little cunt clutching his cock exquisitely tight, choking his length with pulsing muscles.

He can’t handle it, it’s like you’re milking him, cunt fluttering and clamping down while he’s so deep and tight and wet.

“Y/N, oh fuck,” he gasps with his lips at your temple, every muscle of his body stiffens as he finds his release. You can feel it, his semen, just like your cousin told you. It’s warm inside you and then dripping down your thighs as he continues to move, his cock forcing it out and on the couch cushion that you’ll have to wash before your mom gets back.

He falls lax on top of you, his heart beating fast as he tries to catch his breath. You lay there, waiting, unsure of what you’re supposed to, so you run your fingers through his hair until he calms down.

Sam lifts himself up, his softening cock yanking from your cunt when slides back beside you, his arm snaking over your torso. Everything feels wet and sticky, covered in sweat and slick but it’s not bad, just new.

Kissing your cheek he rests his head beside yours, watching as you turn to meet his gaze. “Can I stay here with you tonight?” He asks hopefully.

“Of course, no one’s coming up until tomorrow afternoon.” You feel a heat rise in your cheeks at the thought of him spending the night in your bed. “I need to take a shower…you wanna come with me?” You ask sheepishly.

“Yeah” Sam nods as you both sit up. You stand feeling his come dipping down your thighs and move toward the stairs. Sam tells you, “I gotta call Dean and let him know I won’t be home, I’ll be up in a minute.”

He watches you bound naked up the stairs, waiting until he hears the shower to reach for the house phone. He dials the number to the motel, cupping his soft, wet dick in his hand.

“What is it?” Dean answers, sounding annoyed.

“It’s me, I ah, I’m gonna stay here tonight,” Sam’s flush with embarrassment.

“Sammy!” Dean’s voice perks up, Sam can almost hear the smile in his voice. “Spending the night huh? How’d it go? You do it yet?”

“God Dean,” Sam huffs, looking up the stairs to make sure you aren’t listening, “yeah we did it…I think she liked it.”

“Of course she did,” Dean beams like a proud papa bear, “you do what I told you, that thing with her-”

“Yeah, it worked,” Sam admits.

“Excellent. I wouldn’t steer you wrong…you wrapped it up right?”

“Umm,” Sam hesitates, the condoms his brother gave him crossing his mind for the first time since he got here.

“Sam, please tell me you used protection.” They’re both quiet for a moment before Dean sighs, then chuckles “well it happens, I’m sure it’ll be fine. Just try to remember when you go for round two alright?”

“Sam?” you call for him, cracking open the bathroom door. You’re still naked and he catches a glimpse of your breast.

“Shit Dean, I gotta go, see you tomorrow.”


End file.
